Every Star Reese Witherspoon Has Publicly Dated Over the Years

In a 2015 Reddit AMA, Jeremy Sisto revealed he and Witherspoon dated when they were teenagers. “She was my first actress girlfriend. We had a long-distance relationship for a long time,” he said.

The pair met while filming the movie “Desperate Choices: To Save My Child.” Although Sisto said he was “so into” Witherspoon at the time, their relationship fizzled out due to a misunderstanding. “She went to Africa to do a movie, and I guess I thought she had broken up with me because she didn’t call that much,” Sisto said. “So, I moved on and met my ex-wife Marisa [Ryan]. When [Witherspoon] returned, I found out that wasn’t her intention, but I had already gotten involved. Felt badly.”

Despite what happened, Sisto has nothing but love for Witherspoon. “She’s a great person,” he said.

Witherspoon and Ryan Phillippe met at her 21st birthday party in 1997. During a 1998 interview with Jane magazine, the “Sing 2” star said she was the one who flirted first. “I don’t know what came over me – maybe the seven Midori sours – but I told [Ryan], ‘I think you’re my birthday present,'” she recalled about their first meeting. “He thought it was so flattering, and now that I think about it . . . how embarrassing!”

The pair got engaged in December 1998. Shortly after their movie “Cruel Intentions” premiered in March 1999, Witherspoon and Phillippe got married in June 1999 in South Carolina. The actor gave birth to their daughter, Ava, that September. While Witherspoon and Phillippe’s relationship looked picture perfect, they revealed in 2002 they had begun couple’s therapy to work out certain issues. “The biggest mistake is not doing that, ignoring it, and having the marriage fall apart because of laziness,” Phillippe told the New York Daily News at the time (via People). Witherspoon and Phillippe then welcomed their son, Deacon, in October 2003.

The stars remained together for three more years until they announced their split in October 2006. “We are saddened to announce that Reese and Ryan have decided to formally separate,” a rep for the couple said in a statement. “They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time.” That November, the “Little Fires Everywhere” actor officially filed for divorce, which was finalized in 2008.

Despite their breakup, Witherspoon and Phillippe have maintained a good relationship with each other. While appearing on “The Ellen DeGeneres Show” in May 2010, Phillippe said things between him and his ex-wife had been “great” and they had just been focusing on coparenting. “It is so important as divorced parents to keep that connection. It makes the kids feel better that the parents are interacting,” he said. “We go to all the school events together, and we’re there for each other.”

Witherspoon began dating her “Rendition” costar Jake Gyllenhaal in 2007. A source close to the couple reportedly told People that Gyllenhaal introduced himself to Witherspoon first. Considering she had just broken up with Phillippe, Witherspoon apparently “never” thought she would date Gyllenhaal, but “she just kind of developed this little crush over time.”

The stars seemingly broke up for a short time in the summer of 2007. According to People, their split may have stemmed from Witherspoon wanting to prioritize her family amid her divorce. “Reese was the one who had to do it,” a source reportedly told the publication at the time. “She just got out of a divorce and was so concerned with her family, she just didn’t have the time for [Jake] and he really demanded that.”

It seems Witherspoon just couldn’t say goodbye to Gyllenhaal, because the pair were seen holding hands in Rome that October. Their relationship proved to be back on, and in November 2008, Witherspoon praised Gyllenhaal in an interview with Vogue (via People), calling him “very supportive.”

“Suffice it to say, I’m very happy in life, and I’m very lucky to have a lot of really supportive people around me who care very much for me, and, you know, that’s all you can hope for in life,” she said. “I am very blessed in that way.”

After initially keeping their relationship low-key, the couple made their romance public in 2009 by showing off PDA on several occasions. That year, they kissed at a Lakers game, held hands at the Vanity Fair Oscars party, and cuddled at Coachella. Witherspoon also opened up about their relationship in an interview with InStyle that October. “Jake is a great cook – he does a lot,” she said. “We spend the weekends outside L.A, in Ojai, where I have a farmhouse. We have chickens and we grow cucumbers and tomatoes. I love it. It reminds me of where I grew up in Tennessee.”

By November, rumors began circulating that Witherspoon and Gyllenhaal had called it quits, but reps for both stars apparently denied the breakup. In December, Witherspoon and Gyllenhaal split for real, however. “It broke [Jake’s] heart,” a source told US Weekly at the time. The insider added that the pair “fought constantly in the past few months” and ultimately ended their relationship “over a series of phone calls.”

Just a few weeks after Witherspoon and Gyllenhaal broke up, she met her future husband, Jim Toth, at a party in January 2010. While speaking with Elle in 2012, Witherspoon explained that Toth had actually saved her from an awkward encounter. “It happened out of the blue,” she said. “This really drunk guy was hitting on me, making such an idiot of himself, yelling at me. He was like, ‘You don’t know me.’ And I was like, ‘Yeah, I know. I don’t know you!'”

When Toth noticed what was going on, he came over to Witherspoon and explained that guy was his friend, who had just broken up with someone. “Jim was a really good friend, pulling him out of that situation,” Witherspoon said. “That’s just kind of who he is, a really good person.”

In February 2010, the pair were seen on a date at an Italian restaurant in Santa Monica, per People. A source reportedly told the outlet that Witherspoon and Toth “were very flirtatious throughout dinner” and they were “laughing and talking” the entire time. “Reese seemed very happy. She was smiling all dinner,” the insider said. “The mood was upbeat and really good.”

By that March, it seemed they had officially become an item, because Witherspoon celebrated her birthday with Toth and even introduced him to all of her friends. According to People, Witherspoon then introduced her boyfriend to her kids that April, and they even spent Easter together.

The couple then got engaged in December 2010 after just a year of dating. “Jim knows Reese is the one for him,” a source reportedly told People at the time. “It’s what he’s been waiting for. [Getting engaged] is a natural step for them.” A source close to Witherspoon also reportedly said the actor “quickly realized” Toth was the one because “she felt safe with” him, and he was someone she could “could count on.”

They officially tied the knot in May 2011. Witherspoon and Toth exchanged their vows at her ranch in Ojai, CA, per CBS News. They welcomed their son, Tennessee James Toth, on Sept. 26, 2012.

On March 24, 2023, Witherspoon and Toth announced their decision to separate after nearly 12 years of marriage. In a since-deleted Instagram post, they wrote, “It is with a great deal of care and consideration that we have made the difficult decision to divorce. We have enjoyed so many wonderful years together and are moving forward with deep love, kindness and mutual respect for everything we have created together.” The pair’s final divorce decree was submitted on Aug. 2, according to People.